Chat with us, powered by LiveChat Walking Holidays in Tuscany for Solo Travelers | Guided Walking Tours of Tuscany | Solos

What to expect on your Tuscany walking holiday

Four Guided Walks

Four Guided Walks

Walk through iconic Tuscan landscapes following sections of the Via Francigena

San Gimignano

San Gimignano

Stay in the heart of Tuscany,  surrounded by spectacular views across the Tuscan countryside

Wine Tasting

Wine Tasting

Enjoy wine tasting at Castello di Volpaia a historic wine estate in the heart of the Chianti Classico region

Medieval Hilltop Towns

Medieval Hilltop Towns

Visit beautiful historic towns including Radda in Chianti, Monteriggioni and Asciano

About this trip...

Join a sociable group of solo travellers and discover the very best of Tuscany on foot, combining beautiful countryside, historic hill towns, outstanding food and world-renowned wines. Our base is the beautiful medieval town of San Gimignano, where we’ll enjoy the charm of its famous towers and historic streets. From here, scenic trails lead through the surrounding countryside, taking us to the fortified village of Monteriggioni, the vineyards and olive groves of Chianti, and the rolling landscapes of the Crete Senesi. 
 
Along the way, we’ll experience the region’s rich history and culture, from ancient abbeys to historic estates and wineries. There are also plenty of opportunities to savour the flavours of the region, including a gelato tasting in San Gimignano and a wine tasting at the beautiful Castello di Volpaia. Perfect for solo travellers, this holiday combines rewarding guided walks with plenty of opportunities to relax, explore and enjoy Tuscany’s famous cuisine in the company of like-minded travellers.
Walking Level: Walking Level
What's this?

What's included?

  • Return transfers (these transfers are time specific)
  • Private room for sole use
  • Breakfast daily, 1 lunch & 2 dinners
  • Gelato tasting
  • Wine tasting
  • Welcome drink & information meeting
  • 4 guided walks
  • Free Solos App with all your travel documents
  • Dedicated WhatsApp group for your trip
  • Accompanying Solos Tour Leader

What's Extra

  • Domestic and or International flights are not included
  • Let us help you book them! Learn more.
  • Private Airport transfers 
  • Travel insurance
  • Tips & drinks
  • Meals when not included in the itinerary
  • Activities when not included in the itinerary
  • Tourist Tax €3.00 per night (payable locally)

Itinerary

  • Arrival Day
  • San Gimignano Loop
  • Radda to Volpaia
  • At Leisure
  • Strove to Monteriggioni
  • Asciano Loop
  • At Leisure
  • “Arrivederci”

What you'll be doing

Day One: Arrival Day

Day One: Arrival Day

We arrive into Pisa and transfer to our hotel in San Gimignano where we can meet each other and enjoy a welcome drink and dinner at a local restaurant. 
  • Dinner included
Day Two: San Gimignano Loop

Day Two: San Gimignano Loop

Set out from our hotel on a scenic circular walk through the beautiful Tuscan countryside. Our route follows quiet country tracks and sections of the historic Via Francigena, winding through rolling hills, vineyards and olive groves. As we walk away from the town, enjoy wonderful views back towards San Gimignano and its distinctive medieval towers, before the route loops through the peaceful countryside around Monteliveto, Santa Lucia and Aiano.
Lunch will be enjoyed at a local restaurant, before returning to San Gimignano for a guided tour of the town, discovering its historic streets, impressive towers and fascinating heritage. We'll finish with a gelato tasting at a world-renowned, award-winning gelateria, the perfect way to round off our day.
  • Distance: 8km/5 miles
  • Duration: 3-4hrs approx.
  • Ascent: 215m+/705ft+
  • Terrain: A mixture of quiet country lanes, unpaved tracks and well-established trails, with some uneven and gently undulating sections. Expect a few moderate climbs and descents through vineyards, olive groves and rolling Tuscan countryside.
  • Breakfast & lunch included
Day Three: Radda to Volpaia

Day Three: Radda to Volpaia

After breakfast, we depart for the charming hilltop village of Radda in Chianti. From here we'll walk through the spectacular landscapes of the Chianti Classico region towards the medieval village of Volpaia. The route follows quiet gravel tracks and country paths through rolling vineyards, olive groves and shady woodland, with beautiful panoramic views across the surrounding Tuscan hills. Along the way, pass historic farmhouses and traditional Chianti vineyards before the route climbs gently towards Volpaia, where the ancient fortified village and its castle provide a wonderful reward at the end of the walk.

Enjoy a memorable wine tasting at the historic Castello di Volpaia. Discover the fascinating history of the estate as we explore its unique cellars, hidden within the medieval walls, before sampling a selection of Volpaia's renowned wines accompanied by its extra virgin olive oil. With its beautiful setting, centuries-old winemaking heritage and exceptional Sangiovese-led wines, this is a wonderful opportunity to experience the flavours and traditions of Tuscany at their source.
  • Transfer Time: 1hr + 1hr 
  • Distance: 6km/3.7 miles
  • Duration: 2-3hrs approx.
  • Ascent: 215m+/705ft+
  • Terrain: A mix of paved paths, quiet roads, and well-maintained woodland trails, with some uneven ground, gentle inclines, and steps.
  • Breakfast included
Day Four: At Leisure

Day Four: At Leisure

Today is ours to enjoy San Gimignano at our own pace. Explore its atmospheric medieval streets and historic towers, browse the local shops and cafés, or simply relax and soak up the beautiful Tuscan surroundings.

  • Breakfast included

Day Five: Strove to Monteriggioni

Day Five: Strove to Monteriggioni

After breakfast, we’ll travel by bus to the charming village of Strove, where we’ll begin our walk through the peaceful Tuscan countryside towards the medieval walled village of Monteriggioni. Following quiet country lanes and rural tracks, the route winds through the rolling landscapes of the Val d’Elsa, passing vineyards, olive groves and woodland along the way. We’ll also visit the atmospheric village of Abbadia a Isola, with its historic abbey, before continuing through the beautiful countryside to Monteriggioni, one of Tuscany’s best-preserved medieval fortified villages.

  • Transfer Time: 30mins + 35mins
  • Distance: 6.5km/4 miles
  • Duration: 2-3hrs approx.
  • Ascent: 100m+/328ft+
  • Terrain: A mixture of quiet country lanes, gravel tracks and rural paths, with generally gentle, rolling terrain. Expect some uneven and unpaved sections as the trail passes through vineyards, olive groves and woodland, with a few gentle climbs and descents along the way.
  • Breakfast included
Day Six: Asciano Loop

Day Six: Asciano Loop

Today we depart for the historic town of Asciano to explore the beautiful Crete Senesi, one of Tuscany’s most distinctive landscapes, on a scenic circular walk. Our route passes through the rolling countryside, characterised by gently undulating hills, cultivated fields and classic Tuscan scenery, before visiting Asciano, a charming medieval town rich in history and character. We’ll also visit the magnificent Abbazia di Monte Oliveto Maggiore, a peaceful Benedictine monastery set amid woodland and countryside, renowned for its impressive Renaissance frescoes and beautiful setting.

  • Transfer Time: 1hr + 1hr
  • Distance: 6km/3.7 miles
  • Duration: 2-3hrs approx.
  • Ascent: 100m+/328ft+
  • Terrain: A mixture of quiet country lanes, gravel tracks and rural paths, with gentle undulations. Expect some uneven and unpaved sections as the trail passes through the open landscapes of the Crete Senesi, with a few gentle climbs and descents along the way.
  • Breakfast included
Day Seven: At Leisure

Day Seven: At Leisure

After breakfast at the hotel, enjoy another free day exploring San Gimignano. Visit the impressive Duomo and climb Torre Grossa for panoramic views across the Tuscan countryside, or simply relax over a leisurely lunch, sample the local Vernaccia wine and enjoy a gelato in one of the town’s beautiful piazzas.

  •  Breakfast & dinner included

Day Eight: “Arrivederci”

Day Eight: “Arrivederci”

Today we check-out of our hotel and say goodbye before transferring back to Pisa airport for our flight home.

  • Breakfast included

Accommodations

Relais Santa Chiara, San Gimignano

Set just outside the medieval walls of San Gimignano, Relais Santa Chiara is a charming four-star hotel offering a peaceful Tuscan retreat within easy walking distance of the historic centre. Surrounded by beautiful gardens and rolling countryside. With its combination of traditional Tuscan character, countryside views and convenient location, Relais Santa Chiara is an ideal base for exploring San Gimignano and the wider Tuscan region.
Facilities Include:
Enjoy a range of facilities designed for a relaxing stay, including an outdoor swimming pool with panoramic views of the Tuscan countryside, a beautiful Mediterranean garden and outdoor relaxation areas. The hotel also features the I Cipressi Bistrot, offering drinks, snacks and light meals, as well as breakfast service.
Room Includes:
Rooms are equipped with Wi-Fi, TV, minibar, air conditioning, safe, tea and coffee making facilities and hairdryer. 

Dates & Prices

Departure Return Nights Price from Other Info
Oct 2 2027 Oct 9 2027 7
$3209
+approx. $22.34 local fees
 

Essential Information

Transfer Time
The transfer time from Pisa Airport to San Gimignano is approximately 1hr 10mins depending on traffic.
Airport Transfers

Complimentary group airport transfers are included on arrival and departure days within specific time windows. If your flight falls outside these times, or if you prefer a private airport transfer, these are available for an additional fee. Our team can advise you of the departure times for the group shuttle. To learn more about flight options, payments, and transfers, click here.

Gratuities
We suggest a Group Collection to cover transfer drivers, and hotel staff of €25.00 per person. Your Tour Leader will collect this on your behalf and distribute it accordingly, thus relieving you of the burden of who, when and how much to tip. The tipping of housekeeping will be left to your individual discretion (a small amount left in your room on departure should cover this and would be much appreciated). As is customary, ‘the hat’ will be passed around for the driver and guide on all optional excursions. For any meals that are not included in your itinerary, or taxi fares, your Tour Leader can advise of an appropriate add on. 
Flights

Whether you'd like us to arrange your flights or prefer to book your own, we're here to make the process easy. Our team can secure flights from the location that suits you best, or provide all the arrival and departure details you'll need if booking independently.

Travel Insurance
We strongly recommend purchasing travel insurance before any trip — it safeguards you against unexpected issues like illness, cancellations, or lost luggage. It also protects your health and travel investment, giving you peace of mind to fully enjoy your journey. Click here. to learn more.
WhatsApp Group

Shortly before your holiday, you will be invited to join an optional WhatsApp group to connect with your fellow travellers and your Tour Leader.

What to Wear - Walking Days

It is important that you have the correct footwear. It is essential to wear walking boots that are comfortable and preferably lightweight, with some ankle support and a good grip. If you already have a pair of boots that you are happy walking in (including during hot/wet weather and on hard ground), then bring these along. However, if you are bringing new footwear, do make sure they are well broken in before you arrive. The weather, even in summer, can be unpredictable. We would therefore recommend you travel with clothing suitable for all conditions, and suggest you use the following checklist as a guideline of what to take:

  • Walking boots with good ankle support
  • Waterproofs – jacket and trousers
  • Walking poles – recommended as they provide good support for the knees, particularly on downhill sections of walks and when conditions are wet/slippery
  • Lightweight trousers and shorts with pockets
  • Shirts or t-shirts for walking in
  • Walking socks – several pairs
  • Lightweight fleece or jumper
  • Hat & gloves
  • Daysack/rucksack for walking
  • Umbrella – it can be used also for protection from the sun as well as rain
  • Lightweight drinking bottle to carry water whilst walking
  • Small first aid kit – plasters, insect repellant, etc
  • Good, high factor sunscreen, sunhat and sunglasses – the sun’s strength is often multiplied in mountainous areas.
Walking Programme

Guided walks are included as part of this trip. Your dedicated walking guide will brief you in resort on the daily walking programme.

The walking programme is graded by difficulty, and you can expect to walk varying distances with a range of ascents and descents. Some walks may be challenging, with uneven or rough terrain underfoot and sections at higher altitude. Please refer to the day-by-day itinerary for full details of each walk.

A good level of physical fitness is required to fully enjoy this trip.

It is important that you consider whether your chosen trip is suitable for your level of fitness, mobility and any medical conditions or additional needs. If you are unsure, please contact our team before booking. We will be happy to discuss the trip requirements and your individual circumstances to help you decide whether the trip is suitable for you.

We are committed to treating all customers fairly and will consider any reasonable adjustments where possible. Please let us know before booking if you have a disability, medical condition or any additional requirements that may affect your trip. This allows us to assess whether we can safely and appropriately accommodate your needs and to ensure you have the best possible trip experience.

Care should be taken at all times, particularly on uneven or wet terrain. If you normally use walking poles, we recommend bringing them with you. Sturdy walking boots or walking shoes are essential.

Please note that the route and content of the walking programme may need to change during the trip, at the discretion of the specialist walking guide or local organiser, if local conditions require.

If you have any concerns during your trip, please speak to your specialist walking guide or Solos Tour Leader.

For further information, please refer to our website Terms and Conditions 

Passports and visas

We recommend that you check passport and visa requirements for the country you are visiting at the State Department if you have a U.S. Passport. Most countries require that your passport have at least six months validity when traveling internationally, and many require that you have one to two blank visa pages for either an entry stamp or visa. As a general rule, please check that your passport has six months validity beyond your planned trip, and if not, please renew your passport with plenty of time to provide Solos with your updated passport information by the final payment due date.

Not sure what travel documents you need? Our trusted partner, sherpa°, makes it easy to check visa and entry requirements based on your destination and passport. One quick check now means smooth sailing later. Click here to learn more.

Health requirements 
We recommend that you check if vaccinations are required for your destination at the CDC’s recommendations for your visited destination(s). We also recommend you purchase travel protection. A travel protection plan can often assist with medical emergencies and reimburse costs that are covered by the plan. Please verify coverage details with Solos before you travel.
Time Difference
Italy is 6 hours ahead of EST.
 
Electrical Appliances

Voltage 230v
Travel adaptor type C (EuroPlug)

Rated as Excellent (4.8/5) by our customers

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Fantastic time

I’ve recently returned from my first Solos trip and had a fantastic time. I can honestly say that I enjoyed every minute, and the memories will last a lifetime.
-Patricia

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Highly Recommended

I’d highly recommend Solos to people looking to travel on their own with a group of like minded people.
-David

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Brilliant Week!

We laughed until our bellies ached. It was such a brilliant week.
-Janev

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Go for it!

I still get a bit nervous but this will be my third time with Solos and its one of the best decisions I have ever made- everyone is so friendly, just go for it!!
-Jane

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